CN106980230B - Photosensitive resin composition, color filter using the same, and display device - Google Patents
Photosensitive resin composition, color filter using the same, and display device Download PDFInfo
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- CN106980230B CN106980230B CN201610890509.7A CN201610890509A CN106980230B CN 106980230 B CN106980230 B CN 106980230B CN 201610890509 A CN201610890509 A CN 201610890509A CN 106980230 B CN106980230 B CN 106980230B
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- Prior art keywords
- photosensitive resin
- resin composition
- photopolymerization initiator
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- meth
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- 239000011342 resin composition Substances 0.000 title claims abstract description 95
- 239000003999 initiator Substances 0.000 claims abstract description 60
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 150000002923 oximes Chemical class 0.000 claims abstract description 17
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 12
- 239000011159 matrix material Substances 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000003086 colorant Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 150000008064 anhydrides Chemical group 0.000 claims description 6
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000011247 coating layer Substances 0.000 claims description 3
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 abstract description 17
- 230000018109 developmental process Effects 0.000 abstract 1
- 230000007261 regionalization Effects 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 60
- -1 oxime ester compounds Chemical class 0.000 description 42
- 239000000049 pigment Substances 0.000 description 25
- 229920005989 resin Polymers 0.000 description 18
- 239000011347 resin Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- 239000012965 benzophenone Substances 0.000 description 13
- 239000006229 carbon black Substances 0.000 description 13
- 235000019241 carbon black Nutrition 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 12
- 239000004973 liquid crystal related substance Substances 0.000 description 12
- 239000000178 monomer Substances 0.000 description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 239000003822 epoxy resin Substances 0.000 description 9
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 229920000647 polyepoxide Polymers 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000012860 organic pigment Substances 0.000 description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 150000007519 polyprotic acids Polymers 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- JWTGRKUQJXIWCV-UHFFFAOYSA-N 1,2,3-trihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(O)C(O)CO JWTGRKUQJXIWCV-UHFFFAOYSA-N 0.000 description 2
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 2
- FYBFGAFWCBMEDG-UHFFFAOYSA-N 1-[3,5-di(prop-2-enoyl)-1,3,5-triazinan-1-yl]prop-2-en-1-one Chemical compound C=CC(=O)N1CN(C(=O)C=C)CN(C(=O)C=C)C1 FYBFGAFWCBMEDG-UHFFFAOYSA-N 0.000 description 2
- CNJRPYFBORAQAU-UHFFFAOYSA-N 1-ethoxy-2-(2-methoxyethoxy)ethane Chemical compound CCOCCOCCOC CNJRPYFBORAQAU-UHFFFAOYSA-N 0.000 description 2
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- BURSQOWDCOMQCI-UHFFFAOYSA-N 2-methyl-2-morpholin-4-yl-1-phenylpropan-1-one Chemical compound C=1C=CC=CC=1C(=O)C(C)(C)N1CCOCC1 BURSQOWDCOMQCI-UHFFFAOYSA-N 0.000 description 2
- OWUHRZHVNBBSBR-UHFFFAOYSA-N 3-(2-hydroxypropyl)-4-prop-2-enoyloxyphthalic acid Chemical compound C(C=C)(=O)OC=1C(=C(C(C(=O)O)=CC=1)C(=O)O)CC(C)O OWUHRZHVNBBSBR-UHFFFAOYSA-N 0.000 description 2
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 2
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- FFOPEPMHKILNIT-UHFFFAOYSA-N Isopropyl butyrate Chemical compound CCCC(=O)OC(C)C FFOPEPMHKILNIT-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000006231 channel black Substances 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- LPEKGGXMPWTOCB-UHFFFAOYSA-N methyl 2-hydroxypropionate Chemical compound COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 2
- XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 238000000206 photolithography Methods 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
- OJLABXSUFRIXFL-UHFFFAOYSA-N (2-benzoylphenyl)-phenylmethanone Chemical compound C=1C=CC=C(C(=O)C=2C=CC=CC=2)C=1C(=O)C1=CC=CC=C1 OJLABXSUFRIXFL-UHFFFAOYSA-N 0.000 description 1
- AWLBWXKHTDJKBH-UHFFFAOYSA-N (3-methoxy-3-methylbutyl) acetate 5-methoxy-5-methylhexanoic acid Chemical compound CC(CCCC(=O)O)(C)OC.C(C)(=O)OCCC(C)(OC)C AWLBWXKHTDJKBH-UHFFFAOYSA-N 0.000 description 1
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- XLYMOEINVGRTEX-ONEGZZNKSA-N (e)-4-ethoxy-4-oxobut-2-enoic acid Chemical compound CCOC(=O)\C=C\C(O)=O XLYMOEINVGRTEX-ONEGZZNKSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- QWOZZTWBWQMEPD-UHFFFAOYSA-N 1-(2-ethoxypropoxy)propan-2-ol Chemical compound CCOC(C)COCC(C)O QWOZZTWBWQMEPD-UHFFFAOYSA-N 0.000 description 1
- MAQLWWPSJDSHIT-UHFFFAOYSA-N 1-(4-hexylphenyl)-2-methyl-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(CCCCCC)=CC=C1C(=O)C(C)(C)N1CCOCC1 MAQLWWPSJDSHIT-UHFFFAOYSA-N 0.000 description 1
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- BRXKVEIJEXJBFF-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)-3-methylbutane-1,4-diol Chemical compound OCC(C)C(CO)(CO)CO BRXKVEIJEXJBFF-UHFFFAOYSA-N 0.000 description 1
- PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 description 1
- KBOHXEQLUYXDLA-UHFFFAOYSA-N 2-(2-benzoylphenyl)-1-phenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1C(=O)C1=CC=CC=C1 KBOHXEQLUYXDLA-UHFFFAOYSA-N 0.000 description 1
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- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- ILPVOWZUBFRIAX-UHFFFAOYSA-N propyl 2-oxopropanoate Chemical compound CCCOC(=O)C(C)=O ILPVOWZUBFRIAX-UHFFFAOYSA-N 0.000 description 1
- HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butyrate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-UHFFFAOYSA-N 0.000 description 1
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- 239000000376 reactant Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000006234 thermal black Substances 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Images
Classifications
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
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- G—PHYSICS
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- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133514—Colour filters
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- G—PHYSICS
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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- G—PHYSICS
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
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- G—PHYSICS
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
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- G—PHYSICS
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
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Abstract
The invention provides a photosensitive resin composition which has good sensitivity and can inhibit pattern formation undercut after development even if the photosensitive resin composition contains a light-shading agent or the exposure is insufficient, and a color filter and a display device using the photosensitive resin composition. The invention uses a photosensitive resin composition which contains (A) a photopolymerizable compound and (B) an oxime photopolymerization initiator represented by the following general formula (1), and further contains (C) a photopolymerization initiator different from the component (B).
Description
The application is as follows: day 2, 2012, day 17, application No.: 201210036333.0, title of the invention: a photosensitive resin composition, a color filter using the same and a display device are filed separately.
Technical Field
The present invention relates to a photosensitive resin composition, a color filter and a display device using the same.
Background
A display device such as a liquid crystal display has a structure in which a liquid crystal layer is sandwiched between two substrates on which electrodes are formed to face each other and form a pair. A color filter including pixel regions of respective colors such as red (R), green (G), and blue (B) is formed on the inner side of one substrate. The color filter is generally provided with a black matrix tube for dividing each pixel region of red, green, and blue colors.
The color filter is generally manufactured by a photolithography (photolithography) method. That is, a black photosensitive resin composition is first applied onto a substrate, dried, and then exposed and developed to form a black matrix tube. Next, the photosensitive resin composition of each color, such as red, green, and blue, is repeatedly coated, dried, exposed, and developed to form pixel regions of each color at specific positions, thereby manufacturing a color filter.
The black matrix picture tube is a pattern made of a photosensitive resin composition containing a light-shading agent, and can improve the contrast of a display device and obtain good color rendering properties by suppressing light leakage in pixel regions of each color. As described above, the black matrix picture tube formed in the initial stage of manufacturing the color filter has the following functions: after formation, a recess for fitting a photosensitive resin composition for coloring each color pixel region is formed, and each color pixel region is formed at a specific position.
In recent years, in the manufacture of liquid crystal displays, attempts have been made to improve the light-shielding property of black matrix display tubes and to further improve the contrast of images displayed on the liquid crystal displays. Therefore, it is necessary to add a large amount of a light-shading agent to a photosensitive resin composition for forming a black matrix display tube. However, if a large amount of a light-shading agent is added to the photosensitive resin composition, light for curing the photosensitive resin composition hardly reaches the bottom of a film when the film of the photosensitive resin composition formed on a substrate is exposed, and curing failure is caused by a rapid decrease in sensitivity of the curable resin composition.
The photosensitive resin composition is cured by exposing a photopolymerization initiator contained as a partial component of the photosensitive resin composition to light to generate radicals, and polymerizing a polymerizable compound contained in the photosensitive resin composition with the radicals. Therefore, it is known that the kind of photopolymerization initiator contained in the photosensitive resin composition has an influence on the sensitivity of the photosensitive resin composition. In addition, in recent years, as the number of production stages of liquid crystal displays has increased, the number of color filters produced has also increased, and from the viewpoint of further improving productivity, there is a demand for a highly sensitive photosensitive resin composition capable of forming a pattern at a low exposure amount. Under such circumstances, patent documents 1 and 2 propose oxime ester compounds having a cycloalkyl group as photopolymerization initiators capable of improving the sensitivity of photosensitive resin compositions. In examples described in patent documents 1 and 2, compounds represented by the following chemical formulae (a) and (b) (patent document 1) and the following chemical formulae (c) and (d) (patent document 2) are specifically disclosed.
[ solution 1]
Patent document 1: published patent application No. 101565472 of the people's republic of China
Patent document 2: published patent application No. 101508744 of the people's republic of China
Disclosure of Invention
The highly sensitive photosensitive resin composition can be produced by using the compounds represented by the above chemical formulas (a) to (d) as a photopolymerization initiator. However, the present inventors have found that when a black matrix picture tube is formed using these compounds as a photopolymerization initiator, the black matrix picture tube has good sensitivity, but the pattern shape of the formed black matrix picture tube has the following problems.
In general, when a pattern for a color filter of a liquid crystal display is formed using a photosensitive resin composition, the cross section 1 of the pattern in the width direction is generally a trapezoid as shown in fig. 1(a), and the trapezoid has a shape in which the width is wider as it is closer to the bottom side 1a and narrower as it is closer to the top side 1 b. At this time, an angle θ formed between the cross section 1 of the pattern and the color filter substrate (not shown) is an acute angle.
However, if a black matrix tube is formed using a photosensitive resin composition containing compounds represented by the above chemical formulas (a) to (d) as a photopolymerization initiator, then, as shown in fig. 1(b), a part of the bottom of the pattern may be dissolved during development, and undercuts 21 may be formed at both ends of the bottom 2a of the cross section 2, which is a cross section of the pattern in the width direction. At this time, an angle θ formed between the cross section 2 of the pattern and the color filter substrate (not shown) is an obtuse angle. Thus, if the angle θ is an obtuse angle, bubbles are locally generated in the undercut 21 when pixel regions of respective colors such as red, green, and blue adjacent to the black matrix picture tube are formed. That is, when a film of the photosensitive resin composition is formed adjacent to the black matrix picture tube to form the pixel region, the photosensitive resin composition is not mixed into the space where the undercut 21 exists, and the space remains as air bubbles. If such air bubbles are present in the color filter, picture quality of the liquid crystal display device is seriously impaired, thus becoming a problem. This problem occurs significantly in the case of over-development (オーバー) which is a phenomenon where there is some excess of development in forming the pattern for a black-matrix picture tube.
The present invention has been made in view of the above circumstances, and an object thereof is to provide a photosensitive resin composition which has good sensitivity and can suppress pattern undercut after development even when the photosensitive resin composition contains a light-shielding agent or the amount of exposure is insufficient, and a color filter and a display device using the photosensitive resin composition.
As a result of intensive studies to solve the above problems, the present inventors have found that by using an oxime ester compound represented by the following general formula (1) in combination with another photopolymerization initiator, pattern undercut can be suppressed while maintaining good sensitivity obtained by using the oxime ester compound, and have completed the present invention.
A first embodiment of the present invention is a photosensitive resin composition containing (a) a photopolymerizable compound and (B) an oxime photopolymerization initiator represented by the following general formula (1), and further containing (C) a photopolymerization initiator different from the component (B).
[ solution 2]
(in the general formula (1), l is an integer of 1 to 5, m is an integer of 0 to (l +3), n is an integer of 1 to 8, R1Is an alkyl group having 1 to 11 carbon atoms which may have a substituent or an aromatic group which may have a substituent, R2Is any one of substituents represented by the following general formulae (2) to (4), R3Is an alkyl group or an aryl group having 1 to 11 carbon atoms. )
[ solution 3]
(in the above general formulae (2) and (3), R4Is an optionally substituted aromatic group, R5Is a hydrogen atom or an alkyl group or an aryl group having 1 to 10 carbon atoms and having a substituent. In the above general formula (4), R6Is an aromatic group which may have a substituent. )
In addition, a second embodiment of the present invention is a color filter formed using the photosensitive resin composition.
A third embodiment of the present invention is a display device using the color filter.
According to the present invention, it is possible to provide a photosensitive resin composition which has good sensitivity and can suppress undercut of a pattern after development even when the photosensitive resin composition contains a light-shielding agent or the exposure amount is insufficient, and a color filter and a display device using the photosensitive resin composition.
Drawings
FIG. 1 is a schematic view showing a cross-sectional shape of a pattern formed of a photosensitive resin composition in a width direction, (a) is a schematic view showing a cross-sectional shape of a normal pattern, and (b) is a schematic view showing a cross-sectional shape of a pattern in which undercut 21 is formed.
Detailed Description
Photosensitive resin composition
The photosensitive resin composition of the present invention contains at least (A) a photopolymerizable compound, (B) an oxime photopolymerization initiator, and (C) a photopolymerization initiator different from the component (B). Hereinafter, each component contained in the photosensitive composition of the present invention will be described in detail.
[ A ] A photopolymerizable compound
The photopolymerizable compound (a) (hereinafter also referred to as "component (a)") contained in the photosensitive resin composition of the present invention is not particularly limited, and conventionally known photopolymerizable compounds can be used. Among these, resins or monomers having an ethylenically unsaturated group are preferable, and a combination of these is more preferable. By using a resin having an ethylenically unsaturated group and a monomer having an ethylenically unsaturated group in combination, the curability of the photosensitive resin composition can be improved and a pattern can be easily formed.
[ resin having ethylenically unsaturated group ]
Examples of the resin having an ethylenically unsaturated group include: (meth) acrylic acid, fumaric acid, maleic acid, monomethyl fumarate, monoethyl fumarate, 2-hydroxyethyl (meth) acrylate, ethylene glycol monomethyl ether (meth) acrylate, ethylene glycol monoethyl ether (meth) acrylate, glycerol (meth) acrylate, (meth) acrylamide, acrylonitrile, methacrylonitrile, methyl (meth) acrylate, ethyl (meth) acrylate, isobutyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, benzyl (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, butanediol di (meth) acrylate, propylene glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, propylene glycol di (meth) acrylate, oligomers obtained by polymerizing tetramethylolpropane tetra (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, 1, 6-ethylene glycol di (meth) acrylate, cardo-epoxy diacrylate (cardo epoxydiacrylate), and the like; polyester (meth) acrylate obtained by reacting a polyester prepolymer obtained by condensing a polyhydric alcohol with a monobasic acid or a polybasic acid with (meth) acrylic acid; urethane (meth) acrylate obtained by reacting a polyol with a compound having 2 isocyanate groups and then with (meth) acrylic acid; epoxy (meth) acrylate resins obtained by reacting (meth) acrylic acid with epoxy resins such as bisphenol a type epoxy resins, bisphenol F type epoxy resins, bisphenol S type epoxy resins, phenol or cresol novolac epoxy resins, resol type epoxy resins, triphenolmethane type epoxy resins, polycarboxylic acid polyglycidyl esters, polyhydric alcohol polyglycidyl esters, aliphatic or alicyclic epoxy resins, amine epoxy resins, dihydroxybenzene type epoxy resins, and the like. Among epoxy (meth) acrylate resins, those having undergone a polybasic acid anhydride reaction are suitably used. In the present specification, "(meth) acrylic acid" means "acrylic acid or methacrylic acid".
Further, as the resin having an ethylenically unsaturated group, a resin obtained by reacting a reactant obtained by reacting an epoxy compound with an unsaturated group-containing carboxylic acid compound, and further reacting with a polybasic acid anhydride can be suitably used.
Among them, a compound represented by the following formula (a1) is preferable. The compound represented by the formula (a1) is preferable because of its high photocurability.
[ solution 4]
In the formula (a1), X represents a group represented by the following formula (a 2).
[ solution 5]
In the following formula (a2), R1aEach independently represents a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms or a halogen atom, R2aEach independently represents a hydrogen atom or a methyl group, and W represents a single bond or a group represented by the following formula (a 3).
[ solution 6]
In the formula (a1), Y represents a residue obtained by removing an acid anhydride group (-CO-O-CO-) from a dicarboxylic anhydride. Examples of the dicarboxylic anhydride include maleic anhydride, succinic anhydride, itaconic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyl endomethylenetetrahydrophthalic anhydride (methylenetetrahydrophthalic anhydride), chlorendic anhydride, methyltetrahydrophthalic anhydride, and glutaric anhydride.
In the formula (a1), Z represents a residue obtained by removing 2 anhydride groups from a tetracarboxylic dianhydride. Examples of the tetracarboxylic acid dianhydride include pyromellitic anhydride, benzophenone tetracarboxylic acid dianhydride, biphenyl tetracarboxylic acid dianhydride, and diphenyl ether tetracarboxylic acid dianhydride.
In the formula (a1), m represents an integer of 0 to 20.
The acid value of the resin having an ethylenically unsaturated group is preferably 10 to 150mgKOH/g, more preferably 70 to 110mgKOH/g, in terms of the solid content of the resin. It is preferable that the acid value is 10mgKOH/g or more because sufficient solubility in a developer can be obtained. Further, it is preferable that the acid value is 150mgKOH/g or less because sufficient curability is obtained and the surface properties are improved.
The resin having an ethylenically unsaturated group preferably has a mass average molecular weight of 1000 to 40000, more preferably 2000 to 30000. It is preferable that the mass average molecular weight is 1000 or more because good heat resistance and film strength can be obtained. Further, the mass average molecular weight is preferably 40000 or less because good developability can be obtained.
[ monomer having ethylenically unsaturated group ]
The monomer having an ethylenically unsaturated group includes a monofunctional monomer and a polyfunctional monomer.
Examples of the monofunctional monomer include (meth) acrylamide, methylol (meth) acrylamide, methoxymethyl (meth) acrylamide, ethoxymethyl (meth) acrylamide, propoxymethyl (meth) acrylamide, butoxymethoxymethyl (meth) acrylamide, N-methylol (meth) acrylamide, (meth) acrylic acid, fumaric acid, maleic anhydride, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, crotonic acid, 2-acrylamido-2-methylpropanesulfonic acid, tert-butylacrylamide sulfonic acid (tert-butyl acrylamide sulfonic acid), (meth) acrylic acid methyl ester, (meth) acrylic acid ethyl ester, (meth) acrylic acid butyl ester, 2-ethylhexyl (meth) acrylate, Cyclohexyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 2-phenoxy-2-hydroxypropyl (meth) acrylate, 2- (meth) acryloyloxy-2-hydroxypropylphthalate (2- (meth) acryloyloxy-2-hydroxypropylphthalate), glycerol mono (meth) acrylate (glycerol mono (meth) acrylate), tetrahydrofurfuryl (meth) acrylate, dimethylamino (meth) acrylate, glycidyl (meth) acrylate, 2,2, 2-trifluoroethyl (meth) acrylate, 2,2,3, 3-tetrafluoropropyl (meth) acrylate, hemi (meth) acrylate of phthalic acid derivatives, and the like. These monofunctional monomers may be used alone or in combination of 2 or more.
On the other hand, as the polyfunctional monomer, there can be mentioned: ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, butanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, glycerol di (meth) acrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, pentaerythritol di (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, 2, 2-bis (4- (meth) acryloyloxydiethoxyphenyl) propane, 2-bis (4- (meth) acryloyloxypolyethoxyphenyl) propane, 2-hydroxy-3- (meth) acryloyloxypropyl (meth) acrylate, ethylene glycol diglycidyl ether di (meth) acrylate, diglycidyl phthalate di (meth) acrylate, glycerol triacrylate, glycerol polyglycidyl ether poly (meth) acrylate, urethane (meth) acrylate (i.e., benzal diisocyanate), a reaction product of trimethylhexamethylene diisocyanate with hexamethylene diisocyanate and 2-hydroxyethyl (meth) acrylate, methylenebis (meth) acrylamide, a reaction product of dimethylene diisocyanate with dimethylene diisocyanate and 2-hydroxyethyl (meth) acrylate, a reaction product of dimethylene bis (meth) acrylamide, a reaction product of dimethylene bis (meth) acrylate, a reaction product of dimethylene bis (meth, Polyfunctional monomers such as (meth) acrylamide methylene ether and condensates of polyhydric alcohols and N-methylol (meth) acrylamide, and triacrylformal (triacryl formal). These polyfunctional monomers may be used alone or in combination of 2 or more.
The content of the photopolymerizable compound as the component (a) is preferably 10 to 99.9 parts by mass based on 100 parts by mass of the total solid content of the photosensitive resin composition. When the content of the component (a) is 10 parts by mass or more based on 100 parts by mass of the total amount of the solid components, sufficient heat resistance and chemical resistance can be obtained in the formed pattern.
[ B ] Oxime photopolymerization initiator
The oxime photopolymerization initiator (hereinafter also referred to as "component (B)") contained in the photosensitive resin composition of the present invention is a compound represented by the following general formula (1). As described above, in particular, even when a light-shielding agent is contained in a composition such as a photosensitive resin composition for forming a black matrix display tube, the oxime photopolymerization initiator can impart good sensitivity, but on the other hand, undercut may be formed in a formed pattern. The present inventors have found that, in particular, by using an oxime photopolymerization initiator of the following general formula (1) in combination with the following component (C), a photosensitive resin composition can be provided with good sensitivity and generation of undercut in a formed pattern can be suppressed, and have completed the present invention.
[ solution 7]
In the general formula (1), l is an integer of 1 to 5, m is an integer of 0 to (l +3), n is an integer of 1 to 8, R1Is an alkyl group having 1 to 11 carbon atoms which may have a substituent or an aromatic group which may have a substituent, R2Is any one of substituents represented by the following general formulae (2) to (4), R3Is an alkyl group having 1 to 11 carbon atoms or an aryl group. At R1In the case of an alkyl group, preferable examples of the substituent that may be contained include a phenyl group and a naphthyl group. And, in R1In the case of an aromatic group, preferable examples of the substituent that may be contained include an alkyl group having 1 to 5 carbon atoms, an alkoxy group, a halogen atom, and the like.
In the above general formula (1), R is1Preferred examples thereof include methyl, ethyl, propyl, isopropyl, butyl, phenyl, benzyl, methylphenyl and naphthyl, and among them, methyl and phenyl are more preferred. In the above general formula (1), R is3Preferred examples thereof include methyl, ethyl, propyl, isopropyl, butyl, and phenyl groups, and among them, methyl is more preferred.
[ solution 8]
In the above general formulae (2) and (3), R4Is an optionally substituted aromatic group, R5Is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may have a substituent, or an aromatic group. As R4That is, the substituent which the aromatic group may have is preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a halogen atom or the like. And, in R5In the case of an alkyl group, preferable examples of the substituent that may be present include an alkoxy group having 1 to 5 carbon atoms, a phenyl group, and a naphthyl group.
In the above general formulae (2) and (3), R is4Preferred examples thereof include phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2, 3-dimethylphenyl, 2, 4-dimethylphenyl, 2, 5-dimethylphenyl, 2, 6-dimethylphenyl, naphthyl, 2-methoxy-1-naphthyl and 9-anthryl. On the upper partIn the general formulae (2) and (3), R is5Preferred examples thereof include a hydrogen atom, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, n-hexyl group, phenyl group, 3-methylbutyl group, and 3-methoxybutyl group, and among them, ethyl group is more preferred.
In the above general formula (4), R6Is an aromatic group which may have a substituent. At R6That is, the substituent which the aromatic group may have is preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a halogen atom or the like.
As such R6Preferred examples thereof include phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2, 3-dimethylphenyl, 2, 4-dimethylphenyl, 2, 5-dimethylphenyl, 2, 6-dimethylphenyl, naphthyl, p-tert-butylphenyl and p-methoxyphenyl, and among these, more preferred examples thereof include phenyl.
The oxime photopolymerization initiator (B) may be more specifically represented by the following formula.
[ solution 9]
[ solution 10]
The content of the oxime photopolymerization initiator as the component (B) is preferably 0.1 to 50 parts by mass, more preferably 1 to 45 parts by mass, based on 100 parts by mass of the total solid content of the photosensitive resin composition. When the amount is within the above range, sufficient heat resistance and chemical resistance can be obtained, and at the same time, film forming ability is improved and photocuring failure is suppressed.
< photopolymerization initiator (C) different from the above-mentioned component (B) >
The (C) photopolymerization initiator (hereinafter referred to as "component (C)") contained in the photosensitive resin composition of the present invention is a photopolymerization initiator different from the photopolymerization initiator used as the component (B). (C) The component (B) may be any compound other than the component (B), and may be an oxime photopolymerization initiator as in the component (B).
(C) the photopolymerization initiator is not particularly limited as long as it is a compound generating a radical by irradiation with an active energy ray such as an ultraviolet ray or an electron ray, and examples thereof include photopolymerization initiators such as 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone-1, 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-dimethylaminophenyl) butanone-1, 2- (4-methylbenzyl) -2-diethylamino-1- (4-morpholinophenyl) butanone-1, 2-methyl-1-phenyl-2-morpholinopropan-1-one, 2-methyl-1- [4- (hexyl) phenyl ] -2-morpholinopropan-1-one, 2-ethyl-2-dimethylamino-1- (4-morpholinophenyl) butanone-1, 2-methyl-1-phenyl-2-morpholinopropan-1-one, 2-hydroxy-2-methylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-1- (4-morpholinophenyl) butanone-1, 2-trichlorobenzophenone, a photopolymerization initiator such as bis (bromophenyl) -1, 2' -benzoylbenzophenone, a photopolymerization initiator, a bis (2-benzoylbenzophenone-4, a (2-benzoylmethyl) benzophenone, 2-4- (4-bromophenyl) -1- (4-phenylthiobenzophenone-4-phenyl) -1- (4-phenyl) -1-phenyl) -2-1- (4-phenyl) -2-phenyl-2-morpholinopropan-2-1- (4-morpholinophenyl) -1-2-phenyl) -2-morpholinophenyl) -2-morpholinophenyl-2-morpholinopropane-2-morpholinophenyl-2-morpholinophenyl-2-morpholinopropane-2-1-benzophenone-2-1-2-benzophenone-1-2-benzophenone, a-4-1-4-benzophenone, a-4-phenyl-4-benzophenone, a photopolymerization initiator, a (4-phenyl-4-2-phenyl-2-phenylthiobenzophenone-4-phenyl-4-phenyl-2-phenyl-2-4-phenyl-2-4-2-benzophenone-4-benzophenone, a-benzophenone-phenyl-phenylthiobenzophenone, a-phenyl-4-benzophenone, a-4-phenyl-benzophenone, a photopolymerization initiator, a-4-2-benzophenone-4-1-benzophenone-4-phenyl-4-phenyl-1-4-phenyl-4-1-phenyl-4-phenyl-2-phenyl-4-benzophenone-1-4-benzophenone, a-4-2-1-4-benzophenone, a-benzoylmethyl-phenylthiobenzophenone, a-1-phenyl-benzophenone, a-phenyl-1-phenyl-benzophenone, a-phenyl-4-phenyl-2-benzophenone, a-2-phenyl-1-2-benzophenone, a-phenyl-2-benzophenone, a-phenyl-1-benzophenone, a-1-phenyl-benzophenone, a-1-benzophenone.
[ solution 11]
among the above-listed photopolymerization initiators, α -aminoketone-based photopolymerization initiators, benzophenone-based photopolymerization initiators, triazine-based photopolymerization initiators, and carbazole-based photopolymerization initiators can be preferably used, and the above-mentioned photopolymerization initiators can be used alone or in combination of 2 or more.
The content of the component (C) is preferably 0.1 to 50 parts by mass, more preferably 1 to 45 parts by mass, relative to 100 parts by mass of the total solid content of the photosensitive resin composition. The ratio of the component (B) to the component (C) is preferably within a range of 10/1 to 1/10, and more preferably within a range of 10/1 to 1/10, in terms of mass ratio. When the ratio of the component (B) to the component (C) is in the above range, the formation of undercut in a pattern formed by the photosensitive resin composition can be suppressed while maintaining good sensitivity of the photosensitive resin composition.
< (D) colorant
The photosensitive resin composition of the present invention may further contain (D) a colorant (hereinafter also referred to as component (D)). The photosensitive resin composition can be preferably used for forming a color filter of a liquid crystal display, for example, by containing the component (D), i.e., a colorant. The photosensitive resin composition of the present invention contains a light-shading agent as the component (D), and thus can be preferably used for, for example, a black matrix display tube in a color filter forming a display device.
The component (D) contained in The photosensitive resin composition of The present invention is not particularly limited, but for example, a compound classified as a Pigment (Pigment) in color index (C.I.; issued by The Society of Dyers and Colourists Co., Ltd.) is preferably used, and specifically, a colorant having The following color index (C.I.) number can be used.
C.i. pigment yellow 1 (hereinafter, the "c.i. pigment yellow" is the same and therefore only referred to by the reference numeral), 3, 11, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 55, 60, 61, 65, 71, 73, 74, 81, 83, 86, 93, 95, 97, 98, 99, 100, 101, 104, 106, 108, 109, 110, 113, 114, 116, 117, 119, 120, 125, 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 166, 167, 168, 175, 180, 185;
c.i. pigment orange 1 (hereinafter, the "c.i. pigment orange" is the same and is referred to merely as a reference numeral), 5, 13, 14, 16, 17, 24, 34, 36, 38, 40, 43, 46, 49, 51, 55, 59, 61, 63, 64, 71, 73;
c.i. pigment violet 1 (hereinafter, the same as "c.i. pigment violet" and hence the same reference numerals), 19, 23, 29, 30, 32, 36, 37, 38, 39, 40, 50;
c.i. pigment red 1 (hereinafter, the "c.i. pigment red" is the same and is referred to merely as a reference numeral), 2,3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 14, 15, 16, 17, 18, 19, 21, 22, 23, 30, 31, 32, 37, 38, 40, 41, 42, 48: 1. 48: 2. 48: 3. 48: 4. 49: 1. 49: 2. 50: 1. 52: 1. 53: 1. 57 and 57: 1. 57: 2. 58: 2. 58: 4. 60: 1. 63: 1. 63: 2. 64: 1. 81: 1. 83, 88, 90: 1. 97, 101, 102, 104, 105, 106, 108, 112, 113, 114, 122, 123, 144, 146, 149, 150, 151, 155, 166, 168, 170, 171, 172, 174, 175, 176, 177, 178, 179, 180, 185, 187, 188, 190, 192, 193, 194, 202, 206, 207, 208, 209, 215, 216, 217, 220, 223, 224, 226, 227, 228, 240, 242, 243, 245, 254, 255, 264, 265;
c.i. pigment blue 1 (hereinafter, the same as "c.i. pigment blue" and hence the same reference numerals), 2, 15, and 15: 3. 15: 4. 15: 6. 16, 22, 60, 64, 66;
c.i. pigment green 7, c.i. pigment green 36, c.i. pigment green 37;
c.i. pigment brown 23, c.i. pigment brown 25, c.i. pigment brown 26, c.i. pigment brown 28;
c.i. pigment black 1, c.i. pigment black 7.
When the component (D) is used as a light-shading agent, a black pigment is preferably used as the light-shading agent. As the black pigment, there can be mentioned: carbon black, titanium black (titan black), metal oxides, composite oxides, metal sulfides, metal sulfates, metal carbonates, and the like of copper, iron, manganese, cobalt, chromium, nickel, zinc, calcium, silver, and the like, and various pigments which may be organic or inorganic. Among these black pigments, carbon black having a high light-shielding property is preferably used. By using the component (B) and the component (C) in combination as a photopolymerization initiator, it is possible to suppress the formation of undercut in the developed pattern even when a black pigment having high light-shielding properties is used.
As the carbon black, known carbon blacks such as channel black, furnace black, thermal black, and lampblack black can be used, but channel black having excellent light-shielding properties is preferably used. Also, resin-coated carbon black may be used.
Since resin-coated carbon black has lower conductivity than carbon black that is not coated with resin, in the case of using resin-coated carbon black for a black matrix display tube of a liquid crystal display element such as a liquid crystal display, it is possible to produce a display with high reliability and low power dissipation with less occurrence of electric leakage.
The organic pigment may be added as an auxiliary pigment to adjust the color tone of the carbon black.
In order to uniformly disperse the component (D) in the photosensitive resin composition, a dispersant may be further used. As such a dispersant, a polyethyleneimine, urethane resin, or acrylic resin-based polymer dispersant is preferably used. In particular, when carbon black is used as the (D) component, an acrylic resin-based dispersant is preferably used as the dispersant.
The inorganic pigment and the organic pigment may be used singly or in combination of 2 or more, but when used in combination, the organic pigment is preferably used in an amount of 10 to 80 parts by mass, more preferably 20 to 40 parts by mass, based on 100 parts by mass of the total amount of the inorganic pigment and the organic pigment.
The amount of the colorant used in the photosensitive resin composition may be determined as appropriate depending on the use of the photosensitive resin composition, and is, for example, preferably 5 to 70 parts by mass, more preferably 25 to 60 parts by mass, based on 100 parts by mass of the total solid content of the photosensitive resin composition. When the amount is within the above range, the black matrix picture tube or each colored layer can be formed in a desired pattern, which is preferable.
Particularly, when a black matrix picture tube is formed using the photosensitive resin composition, the amount of the light-shading agent in the photosensitive resin composition is preferably adjusted so that the OD value per 1 μm coating layer in the black matrix picture tube becomes 4 or more. When the OD value per 1 μm coating layer in a black matrix display tube is 4 or more, a sufficient display contrast can be obtained in the case of a black matrix display tube used as a liquid crystal display.
Preferably, the component (D) is dispersed at an appropriate concentration using a dispersant, and then added as a dispersion to the photosensitive resin composition.
< other ingredients >
Various additives may be added to the photosensitive resin composition of the present invention as needed. Specific examples thereof include solvents, sensitizers, curing accelerators, photocrosslinkers, photosensitizers, dispersion aids, fillers, adhesion promoters, antioxidants, ultraviolet absorbers, deflocculants, thermal polymerization inhibitors, defoamers, surfactants and the like.
Examples of the solvent used in the photosensitive resin composition of the present invention include: (poly) alkylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol mono-ethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-n-butyl ether, tripropylene glycol monomethyl ether, tripropylene glycol monoethyl ether, etc.; (poly) alkylene glycol monoalkyl ether acetates such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, and propylene glycol monoethyl ether acetate; other ethers such as diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, and tetrahydrofuran; ketones such as butanone, cyclohexanone, 2-heptanone, and 3-heptanone; alkyl lactate esters such as methyl 2-hydroxypropionate and ethyl 2-hydroxypropionate; ethyl 2-hydroxy-2-methylpropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl ethoxyacetate, ethyl glycolate, methyl 2-hydroxy-3-methylbutyrate, 3-methyl-3-methoxybutyl acetate (3-methyl-3-methoxybutyl acetate), 3-methyl-3-methoxybutyl propionate (3-methyl-3-methoxybutyl propionate), ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, n-pentyl formate, isopentyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, isopropyl butyrate, n-butyl butyrate, methyl pyruvate, Other esters such as ethyl pyruvate, n-propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, and ethyl 2-acetoacetate; aromatic hydrocarbons such as toluene and xylene; amides such as N-methylpyrrolidone, N-dimethylformamide and N, N-dimethylacetamide. These solvents may be used alone or in combination of 2 or more.
Among the solvents, propylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, cyclohexanone, and 3-methoxybutyl acetate are preferable because they exhibit excellent solubility in the component (a), the component (B), and the component (C), and the dispersibility of the component (D) can be improved, and propylene glycol monomethyl ether acetate and 3-methoxybutyl acetate are particularly preferably used. The solvent may be appropriately selected depending on the use of the photosensitive resin composition, and examples thereof include: the content of the solvent is about 50 to 900 parts by mass relative to 100 parts by mass of the total solid content of the photosensitive resin composition.
Examples of the thermal polymerization inhibitor used in the photosensitive resin composition of the present invention include hydroquinone, hydroquinone monoethyl ether, and the like. Further, as the defoaming agent, silicone compounds, fluorine compounds, and the like can be cited, and as the surfactant, anionic compounds, cationic compounds, nonionic compounds, and the like can be cited.
Preparation method of photosensitive resin composition
The photosensitive resin composition of the present invention can be obtained by mixing all the above components in a mixer. Further, the photosensitive resin composition may be filtered with a filter to make the photosensitive resin composition uniform.
Method of forming pattern
When the photosensitive resin composition of the present invention is used to form a pattern, the photosensitive resin composition is first applied to a substrate using a contact transfer type application device such as a roll coater, a reverse coater, or a bar coater, or a non-contact type application device such as a spinner (rotary application device) or a curtain flow coater.
Then, the coated photosensitive resin composition is dried to form a coating film. The drying method is not particularly limited, and any of the following methods can be used, for example: (1) drying the mixture on a hot plate at a temperature of 80 to 120 ℃, preferably 90 to 100 ℃ for 60 to 120 seconds; (2) standing at room temperature for several hours to several days; (3) and a method of removing the solvent by placing the sheet in a hot air heater or an infrared heater for several tens of minutes to several hours.
Subsequently, the coating film is irradiated with an active energy ray such as ultraviolet ray or excimer laser through a negative mask to expose a part thereof. The amount of energy rays to be irradiated varies depending on the composition of the photosensitive resin composition, but is preferably, for example, 30 to 2000mJ/cm2Left and right.
Next, the exposed coating film is developed with a developer to form a pattern having a desired shape. The developing method is not particularly limited, and for example, a dipping method, a spraying method, or the like can be used. Examples of the developer include organic substances such as monoethanolamine, diethanolamine, and triethanolamine, and aqueous solutions of sodium hydroxide, potassium hydroxide, sodium carbonate, ammonia, and quaternary ammonium salts. As described above, by using the photosensitive resin composition of the present invention, undercut in a pattern formed after development can be suppressed. Therefore, the use of the photosensitive resin composition of the present invention is preferable because, for example, in the case of producing a color filter used for a display device, entry of air bubbles into the vicinity of the boundary of each pixel can be suppressed.
Subsequently, the developed pattern is preferably post-baked at 200 to 250 ℃.
The thus-formed pattern can be suitably used as a pixel of a color filter or a black matrix tube in a display device such as a liquid crystal display. Such a color filter and a display device using the color filter are also one of the present invention.
[ examples ]
The present invention will be described in further detail with reference to examples below, but the scope of the present invention is not limited to these examples.
[ preparation of photosensitive resin composition ]
Examples 1 to 20 and comparative examples 1 to 15
Photosensitive resin compositions of examples 1 to 20 and comparative examples 1 to 15 were prepared by using compounds of the following formulae B1 to B12 as oxime-based photopolymerization initiators and compounds of the following formulae C1 to C9 as other photopolymerization initiators. Among the oxime photopolymerization initiators represented by the following formulae B1 to B12, the compounds represented by the formulae B1 to B8 correspond to the oxime photopolymerization initiator represented by the general formula (1). The photopolymerization initiators in the photosensitive resin compositions of the examples and comparative examples are shown in tables 1 to 3. In tables 1 to 3, the ratio indicated by the term "oxime/other ratio" indicates the mass ratio of the oxime type photopolymerization initiator to the other photopolymerization initiator in the photopolymerization initiator contained in the photosensitive resin composition.
Each photosensitive resin composition was prepared by the following method: 3-methoxybutyl acetate/cyclohexanone/Propylene Glycol Monomethyl Ether Acetate (PGMEA) was added to a mixture of 100 parts by mass of a photopolymerization initiator (total amount of oximes and other photopolymerization initiators) and 100 parts by mass of the following resin A (solid content 55% by mass, solvent: 3-methoxybutyl acetate), 310 parts by mass of dipentaerythritol hexaacrylate (DPHA, manufactured by Nippon Kagaku K.K.), 175 parts by mass of a carbon black dispersion (carbon black content 20% by mass, CF ブラック, manufactured by Yuguo Kagaku K.) and 450 parts by mass of carbon black dispersion, and the mixture was stirred until the solid content concentration became uniform, so that the solid content was 15% by mass.
The resin A used for preparing the photosensitive resin composition is the same as the resin A-1 described in paragraphs 0063 to 0064 of Japanese patent application laid-open No. 2010-32940.
[ solution 12]
[ solution 13]
[ solution 14]
[ solution 15]
[ Table 1]
[ Table 2]
[ Table 3]
[ evaluation of sensitivity ]
The sensitivity of the photosensitive resin compositions of examples 1 to 20 and comparative examples 1 to 15 was evaluated in accordance with the following procedure. First, a photosensitive resin composition was spin-coated on a glass substrate (10 cm. times.10 cm) and heated at 90 ℃ for 120 seconds to form a 1.0 μm coating film on the surface of the glass substrate. Thereafter, using a mirror projection alignment aligner (product name: TME-150RTO, manufactured by Kogyo トプコン), 50 μm Gap was measured at 3 kinds of 30mJ/cm Gap by using a negative mask having a line pattern of 10 μm width2、60mJ/cm2、120mJ/cm2The coating film is exposed to light at the exposure amount of (3). The exposed film was placed in a 0.04 mass% KOH aqueous solution at 26 ℃ and developed for 50 seconds, then subjected to calcination treatment at 230 ℃ for 30 minutes, and the resultant was measured by a scanning electron microscope to find the density of each of 3 types of the film at 30mJ/cm2、60mJ/cm2、120mJ/cm2Line width of the line pattern formed under the exposure. Using the obtained results, approximation calculation was performed by the least square method from each line width and exposure amount, and the exposure amount for obtaining a line width of 10 μm was calculated. The results are shown in tables 1 to 3 as the sensitivity. The smaller the value of the sensitivity, the higher the sensitivity of the photosensitive resin composition. And, atIn tables 1 to 3, contents of some examples and comparative examples are repeated in order to easily compare the examples and comparative examples.
[ evaluation of Pattern shape ]
Each of the photosensitive resin compositions of examples 1 to 20 and comparative examples 1 to 15 was exposed to light according to the following procedure, and then the pattern shape, which is the presence or absence of undercut of the developed pattern, was evaluated. First, a photosensitive resin composition was spin-coated on a glass substrate (10 cm. times.10 cm) and heated at 90 ℃ for 120 seconds to form a 1.0 μm coating film on the surface of the glass substrate. Thereafter, a mirror projection alignment exposure apparatus (product name: TME-150RTO, manufactured by トプコン Co., Ltd.) was used to expose a substrate to 100mJ/cm of light at an exposure rate of 100mJ/cm through a negative mask having a line pattern with a line width of 10 μm formed thereon2(Gap50 μm) was exposed to light. The exposed film was developed in a 0.04 mass% KOH aqueous solution at 26 ℃ for 50 seconds, then subjected to a firing treatment at 230 ℃ for 30 minutes, and the bonding angle (taper angle) between the pattern and the substrate was measured by a scanning electron microscope. This cone angle corresponds to the angle θ in fig. 1(a) and (b). The measured cone angles are shown in tables 1 to 3. If the cone angle is acute, it means that there is no undercut in the pattern, and if the cone angle is obtuse, it means that there is undercut in the pattern.
As is clear from tables 1 to 3, the photosensitive resin compositions of examples 1 to 20 having the component (B) and the component (C) in the present invention have sensitivity in practical use.
Further, when the photosensitive resin compositions of examples 10, 11, 13, 15 and 16 were compared with the photosensitive resin compositions of comparative examples 7 to 11, it was found that the pattern formed by using the component (B) and the component (C) in combination as a photopolymerization initiator had an acute taper angle, and the undercut of the pattern was effectively suppressed.
Description of the symbols
1 section in width direction of pattern without undercut
2 cross section of undercut Pattern in width direction
Claims (5)
1. A photosensitive resin composition comprising (A) a photopolymerizable compound represented by the following general formula (a1), (B) an oxime photopolymerization initiator selected from the group consisting of compounds represented by the following formulae (B1) to (B8), and (C) a photopolymerization initiator selected from the group consisting of compounds represented by the following formulae (C1) to (C9); the mass ratio of the component (B) to the component (C) is (B)/(C) 50/50-90/10;
[ solution 1]
In the formula (a1), X is a group represented by the following formula (a2), Y is a residue obtained by removing an anhydride group (-CO-O-CO-) from a dicarboxylic anhydride, Z is a residue obtained by removing 2 anhydride groups from a tetracarboxylic dianhydride, and m is an integer of 0 to 20;
[ solution 2]
In the above formula (a2), R1aEach independently represents a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms or a halogen atom, R2aEach independently represents a hydrogen atom or a methyl group, and W is represented by the following formula (a 3);
[ solution 3]
[ solution 4]
[ solution 5]
2. The photosensitive resin composition according to claim 1, further comprising a colorant (D).
3. A photosensitive resin composition for forming a black-matrix picture tube, comprising (A) a photopolymerizable compound, (B) an oxime-type photopolymerization initiator represented by the following general formula (1), (C) a photopolymerization initiator selected from the group consisting of α -aminoketone-type photopolymerization initiator, α -hydroxyketone-type photopolymerization initiator, a benzoin-type photopolymerization initiator, a triazine-type photopolymerization initiator, a carbazole-type photopolymerization initiator, a bisimidazole-type photopolymerization initiator, an oxime-type photopolymerization initiator and a benzimidazoline-type photopolymerization initiator, which is different from the component (B), and (D) a light-shielding agent, wherein the component (D) is contained so that the OD value per 1 [ mu ] m coating layer in the black-matrix picture tube is 4 or more;
[ solution 6]
In the general formula (1), l is an integer of 1 to 5, m is an integer of 0 to (l +3), n is an integer of 1 to 8, R1Is an alkyl group having 1 to 11 carbon atoms which may have a substituent, or an aryl group which may have a substituent, R2Is any one of substituents represented by the following general formulae (2) to (4), R3Is an alkyl group or an aryl group having 1 to 11 carbon atoms;
[ solution 7]
In the above general formulae (2) and (3), R4Is an optionally substituted aromatic radical, R5Is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may have a substituent, or an aromatic group; in the above general formula (4), R6Is an aromatic group which may have a substituent.
4. A color filter formed by using the photosensitive resin composition according to claim 2 or 3.
5. A display device using the color filter according to claim 4.
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| JP2011-036212 | 2011-02-22 | ||
| JP2011036212 | 2011-02-22 | ||
| CN201210036333.0A CN102645843B (en) | 2011-02-22 | 2012-02-17 | Photosensitive polymer combination, colour filter and display device using the photosensitive polymer combination |
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| CN201610890509.7A Active CN106980230B (en) | 2011-02-22 | 2012-02-17 | Photosensitive resin composition, color filter using the same, and display device |
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| JP5793924B2 (en) * | 2011-04-11 | 2015-10-14 | 日立化成株式会社 | Photosensitive resin composition, photosensitive element, method for producing resist pattern, and method for producing printed wiring board |
| KR102130430B1 (en) * | 2012-08-08 | 2020-07-07 | 아사히 가세이 이-매터리얼즈 가부시키가이샤 | Photosensitive film laminate, flexible printed wiring board, and method for manufacturing same |
| KR101968510B1 (en) * | 2013-02-06 | 2019-04-12 | 동우 화인켐 주식회사 | Photosensitive resin composition for forming red pixel pattern |
| KR101852509B1 (en) * | 2013-03-15 | 2018-04-26 | 동우 화인켐 주식회사 | Colored photosensitive resin composition |
| JP6375236B2 (en) * | 2014-02-04 | 2018-08-15 | 新日鉄住金化学株式会社 | Photosensitive composition for light shielding film and cured product thereof |
| JP6401529B2 (en) * | 2014-07-15 | 2018-10-10 | 東京応化工業株式会社 | Photosensitive composition |
| JP2016090797A (en) * | 2014-11-05 | 2016-05-23 | 株式会社Adeka | Curable composition |
| KR101829998B1 (en) * | 2015-11-04 | 2018-02-19 | 롬엔드하스전자재료코리아유한회사 | Colored photosensitive resin composition and light shielding spacer using same |
| JP6788971B2 (en) * | 2016-01-14 | 2020-11-25 | 東京応化工業株式会社 | Photosensitive composition |
| KR101991699B1 (en) | 2016-09-26 | 2019-06-21 | 삼성에스디아이 주식회사 | Photosensitive resin composition, black pixel defining layer using the same and display device |
| JP6785122B2 (en) | 2016-10-24 | 2020-11-18 | 東京応化工業株式会社 | Method for forming a photosensitive composition and a cured film |
| TWI766941B (en) * | 2017-03-31 | 2022-06-11 | 南韓商東友精細化工有限公司 | Blue photosensitive resin composition and color filter and image display device manufactured using the same |
| CN111656277A (en) | 2018-01-31 | 2020-09-11 | 东丽株式会社 | Negative photosensitive resin composition, cured film, element and display device provided with cured film, and method for producing same |
| KR102029733B1 (en) * | 2018-08-23 | 2019-10-08 | 주식회사 삼양사 | photosensitive resin composition |
| JP2021167905A (en) | 2020-04-10 | 2021-10-21 | 東京応化工業株式会社 | Photosensitive composition, patterned cured film production method, and patterned cured film |
| JP2021167906A (en) | 2020-04-10 | 2021-10-21 | 東京応化工業株式会社 | Photosensitive composition, method for producing patterned cured film and patterned cured film |
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| KR20120097462A (en) | 2012-09-04 |
| CN102645843A (en) | 2012-08-22 |
| JP2012189996A (en) | 2012-10-04 |
| TWI536104B (en) | 2016-06-01 |
| KR20170099817A (en) | 2017-09-01 |
| CN102645843B (en) | 2018-05-08 |
| JP6009774B2 (en) | 2016-10-19 |
| KR101851798B1 (en) | 2018-04-24 |
| CN106980230A (en) | 2017-07-25 |
| KR101976268B1 (en) | 2019-05-07 |
| TW201245876A (en) | 2012-11-16 |
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